I'm in favor of doing this or something similar.
There have been other related suggestions for how to make the sequences more accessible, one of which I described here. Instead of re-promoting the old post to the top of the front page, someone could just make a new post (probably in the discussion section) with a link to the old sequence post. The new post could have a standardized format for the title, to make it clear that it's just linking back to the sequences, and perhaps a one paragraph summary of the post that it's linking to.
An advantage of this method is that it's ready to implement - there's no need to program anything new into the site or wait on the folks in charge. We just need to decide on the conventions and then we can start the posts.
I have two specific ideas for what the conventions could be, which I'll leave as comments so that they can be commented on & voted on separately. We could do either one of them, or both.
I think this is a great idea. I've been reading through the sequences and, while I would like to comment, it seems silly to participate in a conversation that occurred two years ago. So the point would be just to have a "fresh" conversation about an old post. I think this is a good idea in general; for some reason the internet likes to pretend that anything written about more than a week ago doesn't exist or isn't relevant.
Given that
1. Deciding to read and actually reading the sequences is 'work'
2. Reading the latest frontpaged article on LessWrong is 'fun'
3. We frequently have gaps in the posting rate of articles that make it to the front page
4. There are many people who joined this community after the sequences were written and haven't gone through all of them
...would it make sense to start bringing articles from the sequences to the front page, either at a set pace or whenever there is a gap in posting?
I have actually read most of the sequences, but wouldn't mind going through them once again. However, taking it up as a project seems like too much work. By bringing an article to the front page, either with the old comment thread or with a fresh one (plus a reference to the old one), it becomes something that the community is doing. Following things that a group you belong to is doing is fun. But for that to happen, we need to share a common pointer to which article is 'the one we are reading now'. Hence, the front page.
In short, I think if people in this community reading (and re-reading) more of the sequences is something we want, then recycling them through the front page is also a good idea.
If the barrier is implementation modifications needed, I may be able to assist.